A practical access to glucose- and allose-based (5+5) 3-spiropseudonucleosides from a common intermediate

Synthesis of EFdA via a Diastereoselective Aldol Reaction of a Protected 3-Keto Furanose

“…Our synthesis of 1 commenced with the oxidation of 7 to ketone 6 (Scheme ). This transformation has previously been effected by the Dess–Martin oxidation, the Swern oxidation, or by reagent systems such as PDC/Ac 2 O, PDC/AcOH, and TEMPO (0.5 mol %)/NaOCl/KBr . After examination of various oxidation conditions, we found that the conversion could be best performed by treating 7 with NaOCl and KBr in CH 2 Cl 2 /aq NaHCO 3 in the presence of a surprisingly small amount (0.005 mol %) of Nor-AZADO ( 8 ) .…”

“…This transformation has previously been effected by the Dess−Martin oxidation, 10 the Swern oxidation, 11 or by reagent systems such as PDC/Ac 2 O, 12 PDC/ AcOH, 13 and TEMPO (0.5 mol %)/NaOCl/KBr. 14 After examination of various oxidation conditions, we found that the conversion could be best performed by treating 7 with NaOCl and KBr in CH 2 Cl 2 /aq NaHCO 3 in the presence of a surprisingly small amount (0.005 mol %) of Nor-AZADO (8). 15 This reaction went to completion within 30 min at 0 °C and could be successfully conducted on a multigram scale (at least up to 100 g).…”

Synthesis of 1,2,3-triazole-linked galactohybrids and their inhibitory activities on galectins

“…24 Copper catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) between azidogalactose 2 and various diynes provided the expected disaccharides 6a-h in good to excellent yields (Scheme1, Table 1). The obtained dimeric structures are characterized by an extended bis(1,2,3-triazol-4-yl)linker.…”

“…The latter was obtained in the diazotransfer reaction using amine 11 and trifluoromethanesulfonyl azide in the presence of catalytic amount of copper(II) sulfate. 24,39 The molecular structure of disaccharide 13 was unambiguously established by its single crystal X-ray analysis ( Figure 2). …”

Crystal structure of 3-deoxy-3-nitromethyl-1,2;5,6-di-O-isopropylidene-α-D-allofuranose

“…The title compound 1, has been used for the syntheses of isoxazoles (Lugiņ ina et al, 2013) and carbohydrate-based amines and amino acids (Rjabovs et al, 2015a). Carbohydrates with amino groups are valuable synthetic precursors and are easily converted to spirocyclic carbohydrate derivatives (Turks et al, 2013), imino sugars , nucleic acid mimetics (Rozners et al, 2003), and azido sugars (Mackeviča et al, 2014;Rjabova et al, 2012). The latter are widely used for the syntheses of triazoles (Uzuleņ a et al, 2015;Grigorjeva et al, 2015) and THF-amino acids (sugar amino acids) .…”